Piperidine → 1,2,3,6-Tetrahydro-4-(3-methoxyphenyl)-1-methylpyridine

HRID 1156996ノート

反応式

HRID 1156996 の反応式
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:15][N:16]1[CH2:21][CH2:20][C:19](O)([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=2)[CH2:18][CH2:17]1.N1CCCC[CH2:31]1.[OH-].[NH4+]>CS(O)(=O)=O>[CH3:15][N:16]1[CH2:21][CH:20]=[C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:31])[CH:23]=2)[CH2:18][CH2:17]1

参加物

6

反応物 4

HCID 8082PiperidineHCID 14812Phosphorus oxide (P4O10)HCID 14923Ammonium HydroxideHCID 205344404-(3-Hydroxyphenyl)-1-methyl-4-piperidinol

生成物 1

HCID 1557781,2,3,6-Tetrahydro-4-(3-methoxyphenyl)-1-methylpyridine

試薬・触媒・溶媒 1

HCID 6395Methanesulfonic Acid溶媒

実験手順

To a stirred solution of 200 ml. of 50 g. of phosphorous pentoxide in methanesulfonic acid was added portionwise over four minutes 59 g. of 1-methyl-4-hydroxy-4-(3-hydroxyphenyl)piperidine. The reaction was exothermic and the temperature rose to 70° C. After complete addition of the piperidine derivative, the reaction mixture was added to 200 g. of ice, and the aqueous mixture was made alkaline by the addition of ammonium hydroxide. The alkaline mixture was extracted several times with diethyl ether, and the ethereal extracts were combined, washed with water, dried, and the solvent was removed by evaporation under reduced pressure to provide 44.7 g. of the product as an oil. The oil thus formed was distilled to provide 1-methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine, B.P. 123°-138° C. at 0.1 torr.

後処理

  1. customrose to 70° C
  2. additionthe reaction mixture was added to 200 g
  3. extractionThe alkaline mixture was extracted several times with diethyl ether
  4. washwashed with water
  5. customdried
  6. customthe solvent was removed by evaporation under reduced pressure
  7. customto provide 44.7 g
  8. customThe oil thus formed
  9. distillationwas distilled

出典と根拠

ORDレコード
ord-6972dab723cc49499acce59436a7ba4d
出典データセット
uspto-grants-1982_06
特許番号
US04337341

反応ノート

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